HCID 59596671, compound → Methyl (2S)-5-(4-{[(2-fluorophenyl)methyl]amino}phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

HRID 2264817Notes

Reaction equation

HRID 2264817 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[CH:12][CH:11]=1)[C:3]([O:5][CH3:6])=[O:4]>[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][NH:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]2[CH2:8][CH2:7][C@@H:2]([C:3]([O:5][CH3:6])=[O:4])[N:1]=2)=[CH:11][CH:12]=1

Participants

3

Reactant 1

HCID 59596671HCID 59596671, compound

Product 1

HCID 59596710Methyl (2S)-5-(4-{[(2-fluorophenyl)methyl]amino}phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylateYield 29.5%

Reagents, catalysts & solvents 1

HCID 76223Silver(I) trifluoromethanesulfonateCatalyst

Procedure

A solution of methyl (2S)-2-amino-5-(4-{[(2-fluorophenyl)methyl]amino}phenyl)-4-pentynoate (D66, 132 mg) and silver triflate (11 mg, 0.045 mmol) was stirred at room temperature 6.5 h. Then silica gel was added and the solvent evaporated. The residue was purified using flash chromatography eluting with a cyclohexanes:ethyl acetate gradient (12%-100%) to afford the title compound (39 mg, 26%). MS: (ES/+) m/z: 327 [MH]+, C19H19FN2O2 requires 326.

Workup

  1. additionThen silica gel was added
  2. customthe solvent evaporated
  3. customThe residue was purified
  4. washeluting with a cyclohexanes

Sources & evidence

ORD record
ord-5a74ca521f4143f680340d3f4c18a25c
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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